Benzamide compound
A compound and formamide technology, applied in the field of benzamide compounds, can solve problems such as undisclosed compounds, and achieve the effect of inhibiting overeating
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manufacture example 1
[0181] 3-Hydroxy-5-isopropoxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide (492mg), potassium carbonate (445mg), N-methylpyrrolidone A solution of 5-chloropyrazine-2-carbonitrile in NMP (3 mL) was added to a mixture of (NMP) (4 mL), followed by stirring at room temperature for 4 hours and at 50° C. for 20 minutes. Diethyl ether (20 mL) and water (20 mL) were added for liquid separation, the organic layer was washed with water (20 mL) and saturated brine (20 mL) successively, and the aqueous layer was extracted with diethyl ether (20 mL) again. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate=1:1~1:2) to obtain 3-[(5-cyanopyrazin-2-yl)oxy]-5 in the form of light yellow oil - Isopropoxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide (632 mg).
manufacture example 2
[0183] 3-[(5-cyanopyrazin-2-yl)oxy]-5-isopropoxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide under ice cooling (615 mg) in methanol (5 mL) was added with 50% aqueous hydroxylamine solution (200 μL), followed by stirring at room temperature for 1 hour. Water (5 mL) was added, and the insoluble material was filtered off and washed with methanol. Drying under reduced pressure gave 3-{[5-(N'-hydroxycarboxamidinyl)pyrazin-2-yl]oxy}-5-isopropoxy-N-(1-methyl- 1H-pyrazol-3-yl)benzamide (618 mg).
manufacture example 3
[0185] 3-{[5-(N'-hydroxycarboxamidinyl)pyrazin-2-yl]oxy}-5-isopropoxy-N-(1-methyl-1H-pyrazol-3-yl ) benzamide (316 mg) was suspended in a mixed solvent of dioxane (2 mL)-chloroform (2 mL), and triethylamine (260 μL), ethyl chloro(oxo)acetate ( 120 μL), and stirred at room temperature for 45 minutes and at 80° C. for 4 hours. The reaction mixture was cooled to room temperature, and triethylamine (64 µL) and ethyl chloro(oxo)acetate (30 µL) were added thereto, followed by stirring at 80°C for 2 hours and at 100°C for 1 hour. The reaction mixture was cooled to room temperature, ethyl acetate and water were added for liquid separation, the organic layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate=1:1~1:2) to obtain 3-(5-{3-isopropoxy-...
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